Disazo dyestuffs having an acylamino group and an aromatic-oxy group on different terminal moieties

ABSTRACT

Disazo dyes of the general formula I ##STR1## where R is an araliphatic or aromatic radical, X 1  is ##STR2## X 2  is hydrogen, phenyl or an aliphatic or araliphatic radical, R 1  is hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, the rings A, B and C may be substituted and the rings B and C may carry a fused benzo ring, and the group ##STR3## may also be a heterocyclic radical of the formula ##STR4## The novel dyes are very suitable for dyeing polyesters and cellulose.

The present invention relates to dyes of the general formula I ##STR5## where R is an araliphatic or aromatic radical, X¹ is ##STR6## X² is hydrogen, phenyl or an aliphatic or araliphatic radical, R¹ is hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, the rings A, B and C may be substituted and the rings B and C may carry a fused benzo ring, and the group ##STR7## may also be a heterocyclic radical of the formula ##STR8##

Examples of radicals R¹ are hydrogen, alkenyl, C₁ -C₁₂ -alkyl which may be interrupted by oxygen and may be substituted by hydroxyl, by chlorine, by bromine, by unsubstituted or substituted carbamyl, by cyano, by C₁ -C₈ -alkoxy, by C₁ -C₈ -alkanoyloxy or by unsubstituted or substituted phenyl, cycloalkyl of 5 to 8 carbon atoms and phenyl which is unsubstituted or substituted by methyl, ethyl or chlorine.

Specific examples of R¹ are hydrogen, CH₃, C₂ H₅, n--C₃ H₇, n--C₄ H₉, n--C₆ H₁₃, CH₂ --CH(C₂ H₅)C₄ H₉ --n, n--C₈ H₁₇, n--C₁₀ H₂₁, n--C₁₂ H₂₅, --C₂ H₄ OCH₂ CH(C₂ H₅)C₄ H₉ --n, CH₂ CH═CH₂, --C₂ H₄ Cl, --C₂ H₄ Br, --C₂ H₄ OCH₃, --C₂ H₄ OC₂ H₅, --C₂ H₄ OC₆ H₅, --C₆ H₁₁, --C₆ H₅, --C₆ H₄ CH₃, --C₆ H₄ Cl, --C₆ H₄ C₂ H₅, --CH₂ --C₆ H₅, --CH₂ --C₆ H₄ --CH₃, --CH₂ C₆ H₄ Cl, --CH₂ C₆ H₃ Cl₂, CH₂ C₆ H₄ NO₂, --CH₂ --C₆ H₄ CN, --C₂ H₄ C₆ H₅, --C₃ H₆ C₆ H₅, C₂ H₄ OC₆ H₅, --C₃ H₆ --CN, --CH₂ --CONH₂, --CH₂ CON(CH₃)₂, CH₂ CON(C₂ H₅)₂, CH₂ CONHC₆ H₅, --CH₂ CO₂ CH₃, --CH₂ CO₂ C₂ H₅, --CH₂ CO₂ C₄ H₉, --CH₂ --CO--CH₃, CH₂ COC₆ H₅, --CH₂ --CH(OH)C₆ H₅, --CH₂ --CH(OH)CH₂ OC₆ H₅, CH₂ CH(OH)C₂ H₅, --C₂ H₄ OCOCH₃, --C₂ H₄ OCOC₃ H₇, --CH₂ CH(C₂ H₅)OCOCH₃, CH₂ CH(C₂ H₅)OCOC₂ H₅, ##STR9## and --C₂ H₄ OC₂ H₄ OC₆ H₅.

The ring B may be substituted by, for example, chlorine, bromine, methyl, ethyl, acetylamino, C₁ -C₄ -alkoxy or phenoxy or may carry a fused benzo ring which is unsubstituted or substituted by methoxy or ethoxy.

Examples of substituents of the ring C are chlorine, methyl, ethyl, methoxy, ethoxy, phenyl and acetylamino.

Examples of substituents of the ring A are chlorine, methyl and C₁ -C₄ -alkoxy.

Examples of araliphatic radicals R are --CH₂ --C₆ H₅, --CH₂ --C₆ H₄ --Cl, --CH₂ --C₆ H₃ Cl₂, --CH₂ --C₆ H₄ NO₂, --CH₂ --C₆ H₄ --CN, --C₂ H₄ --C₆ H₅, --C₃ H₆ --C₆ H₅, --C₂ H₄ --O--C₆ H₅, --C₂ H₄ OC₂ H₄ OC₆ H₅, --CH₂ --CO--C₆ H₅ --CH₂ --CH(CH₃)--C₆ H₅ and --CH₂ --C₆ H₄ --CH₃.

Examples of aromatic radicals R are phenyl and p-chlorophenyl.

A compound of the formula I may be prepared by introducing the radical R by a conventional method into a compound of the formula II ##STR10## For example, for aralkylation of the phenolic OH it is possible to use unsubstituted and substituted aralkyl chlorides and bromides and unsubstituted and substituted diaralkyl sulfates.

The etherification is carried out in a conventional manner, for example in an aqueous alkaline medium, in an aqueous-organic alkaline medium or under anhydrous conditions in an organic solvent in the presence of an acid acceptor. The reaction is most advantageously carried out at from 50° to 160° C., where necessary, in the case of low-boiling solvents, in an autoclave.

A further method of preparation of a dye of the formula I is the conventional acylation of a compound of the formula III ##STR11##

Details of the preparation may be found in the Examples, where parts and percentages are by weight, unless stated otherwise.

Suitable dyeing processes for applying a dye of the formula I are, in particular, those described in German Pat. No. 1,811,796 and German Laid-Open Applications Nos. 2,524,243, 2,528,743 and 2,855,188.

Industrially particularly valuable compounds are those of the general formula I a ##STR12## where B¹ is hydrogen, chlorine, methyl, ethyl, phenyl, methoxy or ethoxy, B² is hydrogen, chlorine or methyl, B³ is hydrogen, chlorine, methyl, ethyl, acetylamino or C₁ -C₄ -alkoxy, B⁴ is hydrogen, methyl or C₁ -C₄ -alkoxy, B³ and B⁴ together may also be a fused benzo ring, B⁵ is hydrogen, methyl, chlorine or C₁ -C₄ -alkoxy, B⁶ is hydrogen, methyl or C₁ -C₄ -alkoxy, X³ is C₁ -C₈ -alkanoyl or benzoyl, X⁴ is hydrogen, C₁ -C₄ -alkyl or phenyl, X³ and X⁴ together may also be a radical of the formula ##STR13## and R has the stated meanings.

Examples of preferred radicals X³ are --COH, --COCH₃, --COC₂ H₅, --COC₃ H₇, --CO₂ CH₃, --CO₂ C₂ H₅ and --CON(CH₃)₂.

Examples of preferred radicals R are CH₂ --C₆ H₅, --CH₂ --C₆ H₄ Cl, --C₂ H₄ --C₆ H₅, --C₂ H₄ O--C₆ H₅, --C₂ H₄ OC₂ H₄ OC₆ H₅, --C₆ H₅ and C₆ H₄ Cl.

The λ_(max) values mentioned in the Examples which follow were measured in dimethylformamide and are in nm.

EXAMPLE 1

33 parts of the dye of the formula ##STR14## 42 parts of potassium carbonate, 51 parts by volume of 2-phenylethyl bromide and 0.4 part of potassium iodide in 225 parts by volume of N-methylpyrrolidone are stirred for 6 hours at 120° C. The batch is poured into 600 parts of methanol, and the product is precipitated with 1,000 parts of water, these operations being carried out at room temperature. After filtering off the product, washing it with water and drying it, 38 parts of the dye of the formula ##STR15## are obtained.

10 parts of this dye are mixed with 100 parts of polyethylene oxide of molecular weight 300 and 790 parts of a 3 percent strength alginate thickener to give an ink; a 65:35 (by weight) polyester/cotton union fabric is printed with this ink by rotary screen printing and is then dried at 100° C. Thereafter, the fabric is treated for 2 minutes with live steam at 200° C., rinsed cold, soaped at the boil, again rinsed cold and dried. A lightfast, washfast, solvent-fast and sublimation-fast yellowish orange print on a white ground is obtained. Printing on a pure cotton fabric gives a similar result.

λ_(max) : 402

EXAMPLE 2

22.8 parts of the dye of the formula ##STR16## 20.9 parts of potassium carbonate and 25 parts of benzyl chloride in 150 parts of N-methylpyrrolidone are stirred for 4 hours at 110° C. 600 parts of methanol are then added to the batch at room temperature, and the precipitate is filtered off, washed with methanol and water and dried. 17 parts of the dye of the formula ##STR17## are obtained.

A fabric of 65 parts of polyester fibers and 35 parts of mercerized cotton is impregnated with a liquor which contains 10 g/l of a 20% strength liquid formulation of the above disperse dye and 80 g/l of a swelling agent and dye solvent comprising a mixture of 3 parts of polyethylene glycol of molecular weight 1,500 and 1 part of an adduct of one mole of neopentanediamine with 15.6 moles of ethylene oxide. The pH of the padding liquor is brought to 6 with glutaric acid. The fabric is impregnated with the padding liquor at a wet pick-up of 45%. It is then dried for 60 seconds at 120° C. and fixed for 90 seconds at 225° C. in a laboratory model of continuous dryer. The fabric is then rinsed cold and warm and washed for 5 minutes at 100° C. in the presence of a commercial detergent. Fixing of the dye to the fabric is virtually complete. A golden yellow dyeing having good lightfastness, wash-fastness and fastness to crocking is obtained.

λ_(max) : 410

EXAMPLE 3

25 parts of the dye of the formula ##STR18## in 100 parts by volume of propionic anhydride containing 2 parts of 4-dimethylaminopyridine are stirred at 110°-120° C. until the starting material is no longer detectable by thin layer chromatography. The product is filtered off at room temperature, washed with methanol and dried under reduced pressure at 60° C. 15.5 parts of the dye of the formula ##STR19## are obtained.

When used in the dyeing process described in the preceding Example, this dye is virtually completely fixed to the fabric. The dyeing is reddish orange and has good lightfastness and washfastness.

λ_(max) : 380

The dyes shown in the Table are obtained similarly and can be used, by the stated methods, to dye and print cotton and union fabrics, on which they give dyeings having good fastness characteristics.

The dyes mentioned in the Tables which follow can be converted to a commercially useful dye formulation as follows: 30 parts of dye, 6 parts of dispersant, 10 parts of humectant, 1 part of disinfectant and about 53 parts of water are milled in a stirred ball until the particle size is about 0.5 μm. The resulting dye dispersion has a good shelf life.

The substituents X¹, X² and T¹ -T⁶ of the dyes listed in the Table which follows, and the positional indices shown in various columns of the Table, correspond to the formula IV ##STR20##

    __________________________________________________________________________     Ex-                                                                            ample                                                                              X.sup.1    X.sup.2                                                                             T.sup.1                                                                            T.sup.2                                                                             T.sup.3                                                                               T.sup.4                                                                            T.sup.5                                                                            T.sup.6     Hue .sup.λ                                                                  max                __________________________________________________________________________     4   COCH.sub.3 CH.sub.3                                                                            H   2-CH.sub.3                                                                          5-CH.sub.3                                                                            2-CH.sub.3                                                                         H   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             403                                                                        yellow                 5   "          "    "   "    "      "   "   OCH.sub.2 CH.sub.2 OC.sub.6                                                    H.sub.5     golden                                                                             403                                                                        yellow                 6   "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.2                                                      H.sub.4 OC.sub.6 H.sub.5                                                                   golden                                                                             402                                                                        yellow                 7   "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5o-Cl                                                              golden                                                                             400                                                                        yellow                 8   "          "    "   "    "      H   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             403                                                                        yellow                 9   "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             402                                                                        yellow                 10  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             402                                                                        yellow                 11  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.4                                                                  golden                                                                             402                                                                        yellow                 12  "          "    "   "    "      "   "   "           golden                                                                             403                                                                        yellow                 13  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.4                                                      CH.sub.3    golden                                                                             402                                                                        yellow                 14  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.4Clp                                                               golden                                                                             403                                                                        yellow                 15  "          "    "   "    "      2-Cl                                                                               5-Cl                                                                               OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             408                                                                        yellow                 16  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             406                                                                        yellow                 17  "          "    "   "    "      3-CH.sub.3                                                                         H   "           golden                                                                             404                                                                        yellow                 18  "          "    "   2-OCH.sub.3                                                                         "      2-CH.sub.3                                                                         "   "           orange                                                                             414                19  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  "   414                20  "          "    "   2-OCH.sub.3                                                                         "      "   "   "           reddish                                                                            485                                                                        orange                 21  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     reddish                                                                            486                                                                        orange                 22  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     reddish                                                                            485                                                                        orange                 23  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.2                                                      H.sub.4 OC.sub.6 H.sub.5                                                                   reddish                                                                            485                                                                        orange                 24  "          H    "   2-CH.sub.3                                                                          "      2-Cl                                                                               "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             411                                                                        yellow                 25  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             410                                                                        yellow                 26  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.2                                                      H.sub.4 OC.sub.6 H.sub.5                                                                   golden                                                                             411                                                                        yellow                 27  "          "    "   "    "      "   "   OCH.sub.2 CH(CH.sub.3)C.sub.6                                                  H.sub.5     golden                                                                             411                                                                        yellow                 28  "          "    "   2-OCH.sub.3                                                                         "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             426                                                                        yellow                 29  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             426                                                                        yellow                 30  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             425                                                                        yellow                 31  "          "    "   2-OCH.sub.3                                                                         "      2-.sup.∴CH.sub.3                                                           H   "           reddish                                                                            486                                                                        orange                 32  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub. 5    reddish                                                                            486                                                                        orange                 33  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  reddish                                                                            486                                                                        orange                 34  "          "    "   "    "      H   "   "           reddish                                                                            484                                                                        orange                 35  "          "    "   "    5-OCH.sub.3                                                                           H   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     reddish                                                                            485                                                                        orange                 36  "          "    "   2-CH.sub.3                                                                          5-CH.sub.3                                                                            2-CH.sub.3                                                                         "   "           golden                                                                             406                                                                        yellow                 37  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             406                                                                        yellow                 38  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             405                                                                        yellow                 39  "          "    "   "    "      H   "   "           golden                                                                             406                                                                        yellow                 40  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             403                                                                        yellow                 41  "          "    "   "    "      "   3-CH.sub.3                                                                         "           golden                                                                             405                                                                        yellow                 42  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             405                                                                        yellow                 43  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             405                                                                        yellow                 44  "          "    "   2-OCH.sub.3                                                                         "      "   "   "           orange                                                                             425                45  "          "    "   "    "      2-CH.sub.3                                                                         H   "           "   426                46  "          "    "   2-CH.sub.3                                                                          5-OCH.sub.3                                                                           "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  "   425                47  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     "   426                48  "          "    "   3-CH.sub.3                                                                          H      "   "   "           golden                                                                             404                                                                        yellow                 49  "          "    "   "    "      H   "   "           golden                                                                             403                                                                        yellow                 50  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             403                                                                        yellow                 51  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             403                                                                        yellow                 52  "          "    "   3-OCH.sub.3                                                                         "      "   "   "           orange                                                                             415                53  "          "    "   2-OCH.sub.3                                                                         "      2-Cl                                                                               5-Cl                                                                               "           "   430                54  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     "   429                55  "          "    "   "    5-CH.sub.3                                                                            3-C.sub.6 H.sub.5                                                                  H   "           golden                                                                             409                                                                        yellow                 56  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             409                                                                        yellow                 57  "          "    "   2-CH.sub.3                                                                          5-CH.sub.3                                                                            "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             408                                                                        yellow                 58  "          CH.sub.3                                                                            "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5Cl(o)                                                 .           golden                                                                             406                                                                        yellow                 59  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             406                                                                        yellow                 60  COC.sub.2 H.sub.5                                                                         H    "   "    "      2-CH.sub.3                                                                         "   "           golden                                                                             403                                                                        yellow                 61  COCH.sub.3 "    "   2-OCH.sub.3                                                                         5-NHCOCH.sub.3                                                                        H   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  reddish                                                                            484                                                                        orange                 62  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     reddish                                                                            484                                                                        orange                 63  "          C.sub.4 H.sub.9n                                                                    "   2-CH.sub.3                                                                          5-CH.sub.3                                                                            "   "   OC.sub.6 H.sub.5                                                                           golden                                                                             402                                                                        yellow                 64  "          CH.sub.3                                                                            "   2-OCH.sub.3                                                                         5-NHCOCH.sub.3                                                                        2-CH.sub.3                                                                         "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     reddish                                                                        orange                 65  "          "    "   2-OC.sub.2 H.sub.5                                                                  5-OC.sub.2 H.sub.5                                                                    "   "   "           reddish                                                                            485                                                                        orange                 66  "          H    "   "    "      "   "   "           reddish                                                                            480                                                                        orange                 67  "          "    "   2-OC.sub.4 H.sub.9                                                                  5-OC.sub.4 H.sub.9                                                                    H   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  reddish                                                                            484                                                                        orange                 68  "          "    Cl  2-CH.sub.3                                                                          5-CH.sub.3                                                                            H   "   "           golden                                                                             403                                                                        yellow                 69  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             403                                                                        yellow                 70  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             403                                                                        yellow                 71  "          "    OCH.sub.3                                                                          "    "      "   "   "           golden                                                                             406                                                                        yellow                 72  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             406                                                                        yellow                 73  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             406                                                                        yellow                 74  "          "    "   2-OCH.sub.3                                                                         "      2-CH.sub.3                                                                         "   "           orange                                                                             421                75  "          "    "   "    "      "   "   "           reddish                                                                            488                                                                        orange                 76  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  reddish                                                                            488                                                                        orange                 77  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     reddish                                                                            488                                                                        orange                 78  "          "    CH.sub.3                                                                           "    "      "   "   "           reddish                                                                            486                                                                        orange                 79  "          "    "   "    5-OCH.sub.3                                                                           "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  reddish                                                                            486                                                                        orange                 80  "          "    "   2-CH.sub.3                                                                          5-CH.sub.3                                                                            "   "   "           golden                                                                             403                                                                        yellow                 81  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             402                                                                        yellow                 82  COC.sub.3 H.sub.6n                                                                        "    H   "    "      H   H   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             403                                                                        yellow                 83  COC.sub.4 H.sub.9n                                                                        "    "   "    "      "   "   "           golden                                                                             403                                                                        yellow                 84  CO.sub.2 CH.sub.3                                                                         "    "   3-CH.sub.3                                                                          H      "   "   "           golden                                                                             403                                                                        yellow                 85  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             402                                                                        yellow                 86  CONHCH.sub.3                                                                              "    "   2-CH.sub.3                                                                          5-CH.sub.3                                                                            2-CH.sub.3                                                                         "   "           golden                                                                             404                                                                        yellow                 87  COCH.sub.3 "    "   "    "      2-Cl                                                                               5-Cl                                                                               OCH.sub.2 COC.sub.6 H.sub.5                                                                golden                                                                             410                                                                        yellow                 88  "          "    "   "    "      "   "   OCH.sub.2 COCH.sub.3                                                                       golden                                                                             410                                                                        yellow                 89  "          "    "   "    "      "   "   OCH.sub.2 CO.sub.2 C.sub.2                                                     H.sub.5     golden                                                                             409                                                                        yellow                 90  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.4                                                      CH.sub.3    golden                                                                             410                                                                        yellow                 91  "          CH.sub.3                                                                            "   "    "      3-CH.sub.3                                                                         H   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             402                                                                        yellow                 92  COC.sub.6 H.sub.5                                                                         H    "   "    "      H   "   "           golden                                                                             405                                                                        yellow                 93  COCH.sub.3 "    "   2-OCH.sub.3                                                                         "      2-CH.sub.3                                                                         "   "           golden                                                                             426                                                                        yellow                 94  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             427                                                                        yellow                 95  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             427                                                                        yellow                 96  "          CH.sub.3                                                                            "   "    "      "   "   "           golden                                                                             414                                                                        yellow                 97  "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             415                                                                        yellow                 98  "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             418                                                                        yellow                 99  COH        H    "   2-CH.sub.3                                                                          "      2-Cl                                                                               5-Cl                                                                               OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             410                                                                        yellow                 100 "          CH.sub.3                                                                            "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             404                                                                        yellow                 101 COCH.sub.3 C.sub.6 H.sub.5                                                                     "   2-OCH.sub.3                                                                         5-OCH.sub.3                                                                           H   H   "           orange                 102 COCH(C.sub.2 H.sub.5)C.sub.4 H.sub.9n                                                     C.sub.2 H.sub.5                                                                     CH.sub.3                                                                           "    "      "   "   "           "   485                103 COC.sub.2 H.sub.5                                                                         C.sub.6 H.sub.5                                                                     H   "    "      "   "   "           "   377                104 "          H    "   2-CH.sub.3                                                                          5-CH.sub.3                                                                            2-Cl                                                                               5-Cl                                                                               "           golden                                                                             411                                                                        yellow                 105 "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             410                                                                        yellow                 106 "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     golden                                                                             411                                                                        yellow                 107 "          "    "   2-OCH.sub.3                                                                         "      2-CH.sub.3                                                                         H   "           orange                                                                             426                108 "          "    "   "    "      H   H   OCH.sub.2 C.sub.6 H.sub.5                                                                  "   425                109 "          "    "   "    5-OCH.sub.3                                                                           H   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     reddish                                                                            486                                                                        orange                 110 "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  reddish                                                                            486                                                                        orange                 111 "          "    "   "    "      "   2-CH.sub.3                                                                         "           reddish                                                                            487                                                                        orange                 112 "          CH.sub.3                                                                            "   2-CH.sub.3                                                                          5-CH.sub.3                                                                            2-Cl                                                                               5-Cl                                                                               "           golden                                                                             405                                                                        yellow                 113 COC.sub.2 H.sub.5                                                                         "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             407                                                                        yellow                 114 CON(CH.sub.3).sub.2                                                                       H    "   "    "      "   "   "           golden                                                                             405                                                                        yellow                 115 CO.sub.2 CH.sub.3                                                                         "    "   "    "      "   "   "           golden                                                                             406                                                                        yellow                 116 COCH.sub.3 CH.sub.2 C.sub.6 H.sub.5                                                            "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             405                                                                        yellow                 117 "          "    "   H    "      H   H   "           golden                                                                             405                                                                        yellow                 118 "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     golden                                                                             405                                                                        yellow                 119 "          CH.sub.3                                                                            "   2-CH.sub.3                                                                          5-OCH.sub.3                                                                           2-CH.sub.3                                                                         "   "           orange                                                                             418                120 "          "    "   2-OCH.sub.3                                                                         "      H   "   "           reddish                                                                            485                                                                        orange                 121 "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  reddish                                                                            485                                                                        orange                 122 "          "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     reddish                                                                            484                                                                        orange                 123 "          C.sub.6 H.sub.5                                                                     "   "    "      "   "   OC.sub.6 H.sub.4p-Cl                                                                       reddish                                                                            380                                                                        orange                 124 "          "    "   "    "      "   "   OC.sub.6 H.sub.5                                                                           reddish                                                                            380                                                                        orange                 125 COC.sub.2 H.sub.5                                                                         "    "   "    "      "   "   "           reddish                                                                            378                                                                        orange                 126 "          "    "   2-CH.sub.3                                                                          5-CH.sub.3                                                                            "   "   "           golden                                                                             376                                                                        yellow                 127 COCH.sub.3 "    "   "    "      "   "   "           golden                                                                             376                                                                        yellow                 128 "          "    "   "    "      "   "   OC.sub.6 H.sub.4p-Cl                                                                       golden                                                                             376                                                                        yellow                 129 "          "    "   2-OCH.sub. 3                                                                        "      "   "   "           orange                                                                             378                130 "          "    "   "    "      "   "   OC.sub.6 H.sub.5                                                                           "   378                131 COC.sub.2 H.sub.5                                                                         "    "   "    "      "   "   "           "   380                132 "          "    "   2-CH.sub.3                                                                          "      "   "   OC.sub.6 H.sub.                                                                            golden                                                                             377                                                                        yellow                 133 COCH.sub.3 "    "   2-OCH.sub.3                                                                         5-OCH.sub.3                                                                           "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  reddish                                                                            380                                                                        orange                 134 "          "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     reddish                                                                            377                                                                        orange                 135 "          "    "   2-CH.sub.3                                                                          5-CH.sub.3                                                                            "   "   "           golden                                                                             376                                                                        yellow                 136 "          "    "   "    "      "   "   OCH.sub.2 C.sub.6 H.sub.5                                                                  golden                                                                             376                                                                        yellow                 137 "          "    "   2-OCH.sub.3                                                                         "      "   "   "           orange                                                                             378                138 COC.sub.2 H.sub. 5                                                                        "    "   "    "      "   "   OC.sub.2 H.sub.4 C.sub.6                                                       H.sub.5     "   378                139 COC.sub.3 H.sub.7                                                                         "    "   "    5-OCH.sub.3                                                                           "   "   OC.sub.2 H.sub.4p-Cl                                                                       reddish                                                                            380                                                                        orange                 140 COCH(C.sub.2 H.sub.5)C.sub.4 H.sub.9 (n)                                                  "    "   "    "      "   "   "           reddish                                                                            380                                                                        orange                 141 "          "    "   "    "      "   "   OC.sub.6 H.sub.5                                                                           reddish                                                                            380                                                                        orange                 142 COH        "    "   "    "      "   "   OC.sub.6 H.sub.4p-Cl                                                                       reddish                                                                            376                                                                        orange                 143 COCH.sub.3 "    "   "    "      "   "   OC.sub.2 H.sub.4 OC.sub.6                                                      H.sub.5     reddish                                                                            378                                                                        orange                 __________________________________________________________________________                         Ex-                                                                            ample                                                                              Formula                         Hue .sup.λ                                                                  max                __________________________________________________________________________                         144                                                                                                                orange                                                                             480                                    145                                                                                 ##STR21##                       "  481                                    146                                                                                 ##STR22##                       "  425                                    147                                                                                 ##STR23##                       "  485                                    148                                                                                 ##STR24##                      golden yellow                                                                      404                                    149                                                                                 ##STR25##                      golden yellow                                                                      402                                    150                                                                                 ##STR26##                      golden yellow                                                                      425                                    151                                                                                 ##STR27##                      reddish orange                                                                     485                __________________________________________________________________________ 

We claim:
 1. A disazo dye of the formula: ##STR28## wherein R is an araliphatic or aromatic radical, X¹ is --CO--R¹, --COOR¹ or --CO--N(R¹)₂, wherein said R¹ radical independently are hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical; X² is hydrogen, phenyl or an aliphatic or araliphatic radical; or X¹ and X² form a heterocyclic radical of the formula ##STR29## rings A, B and C optionally being substituted and rings B and C optionally being fused with a benzo ring.
 2. The disazo dye of claim 1, wherein said amido radical of group X¹ has the formula: --CO--NHR¹, wherein R¹ is as identified above.
 3. The disazo dye of claim 1, of the formula: ##STR30## where B¹ is hydrogen, chlorine, methyl, ethyl, phenyl, methoxy or ethoxy, B² is hydrogen, chlorine or methyl, B³ is hydrogen, chlorine, methyl, ethyl, acetylamino or C₁ -C₄ -alkoxy, B⁴ is hydrogen, methyl or C₁ -C₄ -alkoxy, B³ and B⁴ together may also be a fused benzo ring, B⁵ is hydrogen, methyl, chlorine or C₁ -C₄ -alkoxy, B⁶ is hydrogen, methyl or C₁ -C₄ -alkoxy, X³ is C₁ -C₈ -alkanoyl or benzoyl, X⁴ is hydrogen, C₁ -C₄ -alkyl or phenyl, X³ and X⁴ together may also be a radical of the formula: --CO--(CH₂)₃ --, and R has the stated meanings.
 4. The disazo dye of claim 1, wherein said group R¹ is hydrogen; alkenyl; cycloalkyl of 5 to 8 carbon atoms; phenyl, methyl, ethyl or chloro substituted phenyl; or C₁ -C₁₂ -alkyl optionally interrupted by oxygen or optionally substituted by hydroxyl, chlorine, bromine, carbamyl, substituted carbamyl, cyano, C₁ -C₈ -alkoxy, C₁ -C₈ -alkanoyloxy, phenyl or substituted phenyl.
 5. The disazo dye of claim 4, wherein said radical R¹ is CH₃, C₂ H₅, n--C₃ H₇, n--C₄ H₉, n--C₆ H₁₃, CH₂ --CH(C₂ H₅)C₄ H₉ --n, n--C₈ H₁₇, n--C₁₀ H₂₁, n--C₁₂ H₂₅, --C₂ H₄ OCH₂ CH(C₂ H₅)C₄ H₉ --n, CH₂ CH═CH₂, --C₂ H₄ Cl, --C₂ H₄ Br, --C₂ H₄ OCH₃, --C₂ H₄ OC₂ H₅, --C₂ H₄ OC₆ H₅, --C₆ H₁₁, --C₆ H₅, --C₆ H₄ CH₃, --C₆ H₄ Cl, --C₆ H₄ C₂ H₅, --CH₂ --C₆ H₅, --CH₂ --C₆ H₄ --CH₃, --CH₂ C₆ H₄ Cl, --CH₂ C₆ H₃ Cl₂, CH₂ C₆ H₄ NO₂, --CH₂ --C₆ H₄ CN, --C₂ H₄ C₆ H₅, --C₃ H₆ C₆ H₅, C₂ H₄ OC₆ H₅, --C₃ H₆ --CN, --CH₂ --CONH₂, --CH₂ CON(CH₃)₂, CH₂ CON(C₂ H₅)₂, CH₂ CONHC₆ H₅, --CH₂ CO₂ CH₃, --CH₂ CO₂ C₂ H₅, --CH₂ CO₂ C₄ H₉, --CH₂ --CO--CH₃, CH₂ COC₆ H₅, --CH₂ --CH(OH)C₆ H₅, --CH₂ --CH(OH)CH₂ OC₆ H₅, --CH₂ CH(OH)C₂ H₅, --C₂ H₄ OCOCH₃, --C₂ H₄ OCOC₃ H₇, --CH₂ CH(C₂ H₅)OCOCH₃, --CH₂ CH(C₂ H₅)OCOC₂ H₅, ##STR31## or --C₂ H₄ OC₂ H₄ OC₆ H₅.
 6. The disazo dye of claim 1, wherein radical R is phenyl, p-chlorophenyl, --CH₂ --C₆ H₅, --CH₂ --C₆ H₄ --Cl, --CH₂ --C₆ H₃ Cl₂, --CH₂ --C₆ H₄ NO₂, --CH₂ --C₆ H₄ --CN, --C₂ H₄ --C₆ H₅, --C₃ H₆ --C₆ H₅, --C₂ H₄ --O--C₆ H₅, --C₂ H₄ OC₂ H₄ OC₆ H₅, --CH₂ --CO--C₆ H₅ --CH₂ --CH(CH₃)--C₆ H₅ or --CH₂ --C₆ H₄ --CH₃.
 7. The disazo dye of claim 1, wherein said ring B is substituted by chlorine, bromine, methyl, ethyl, acetylamino, C₁ -C₄ -alkoxy or phenoxy or is fused with a benzo ring optionally substituted by methoxy or ethoxy.
 8. The disazo dye of claim 1, wherein said ring C is substituted by chlorine, methyl, ethyl, methoxy, ethoxy, phenyl or acetylamino.
 9. The disazo of claim 1, wherein said ring A is substituted by chlorine, methyl or C₁ -C₄ -alkoxy. 